Pirates' Top Arms on Deck for Fenway Park Showdown

As the Pittsburgh Pirates (59-76) arrive at Fenway Park to face the Boston Red Sox (75-60) in a three-game series starting Friday, they will line up three starting pitchers — Paul Skenes, Johan Oviedo and Mitch Keller — who are poised to anchor the team’s rotation for the 2026 season. For Pittsburgh, this series not only serves as a test against an opponent that is likely headed to the playoffs, but also offers a glimpse into the Pirates’ future pitching strategy.

Paul Skenes, the Pirates' undisputed ace, will headline the series opener in a highly anticipated pitching duel against Red Sox top prospect Payton Tolle, who is making his MLB debut. Skenes, with an 8-9 record and a stellar 2.07 ERA this season, has been the cornerstone of Pittsburgh’s rotation since he debuted in May 2024.

His performance this season has made him the overwhelming favorite for the National League Cy Young Award, boasting a 0.938 WHIP and 181 strikeouts over 161 innings. He could become the first pitcher to win the Cy Young award with a losing record.

Skenes' last outing was a dominant 7-inning shutout against Colorado on August 24, where he allowed only three hits and struck out seven. The native Californians' consistency and elite stuff have solidified one of the greatest starts to a pitching career that baseball has ever seen, and his matchup against Tolle adds a layer of intrigue to the series.

Mitch Keller, despite an up and down season with a 4.35 ERA and a 6-12 record, remains a key veteran presence. His recent performances have been mixed, including a 6-inning, 3-run outing against St. Louis on August 26, where he struck out nine batters. However, he has a 7.59 ERA in his last seven starts.

Keller’s experience and ability to eat innings (he has logged over 150 innings in four consecutive seasons) make him an easily projectable part of the 2026 rotation. However, his need for greater consistency will be crucial for the Pirates’ future success. It's unlikely that we've heard the last of trade rumors surrounding Keller, and it's entirely possible that he gets dealt this winter.

Johan Oviedo, who missed the entire 2024 season due to elbow surgery, is another veteran poised to play a pivotal role next year. Oviedo’s 2023 campaign was impressive, as he posted 15 starts allowing one or fewer runs and threw a complete-game shutout against Kansas City. His return to full health could provide a significant boost to the Pirates’ rotation next season.

Oviedo will have to hold off plenty of competition next spring. Jared Jones, returning from Tommy John surgery, will slot into the rotation at some point. Braxton Ashcraft and Mike Burrows have also earned the right to compete for a rotation spot, making for an especially competitive spring in Bradenton next year. Prospects like Bubba Chandler and Hunter Barco will also compete for rotation spots.

Chandler has already made a splash, with 8 shutout innings in two relief appearances since making his MLB debut last week. Chandler’s rapid ascent and dominance in the minors (121 strikeouts in 100 innings in Triple-A this year) make him a serious contender for a rotation spot in 2026. It would be a shock if he did not start the season in the rotation.